data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. P. J. Skabara
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C23 H24 O4 S3'
_chemical_formula_sum
 'C23 H24 O4 S3'
_chemical_formula_weight          460.60
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.4623(3)
_cell_length_b                    32.2548(12)
_cell_length_c                    8.4765(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  113.146(2)
_cell_angle_gamma                 90.00
_cell_volume                      2127.42(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4630
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.42
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.16
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.438
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              968
_exptl_absorpt_coefficient_mu     0.377
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8577
_exptl_absorpt_correction_T_max   0.9421
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             19037
_diffrn_reflns_av_R_equivalents   0.0881
_diffrn_reflns_av_sigmaI/netI     0.0870
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -41
_diffrn_reflns_limit_k_max        41
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          27.46
_reflns_number_total              4827
_reflns_number_gt                 3094
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_computing_publication_material   ? 
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0407P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4827
_refine_ls_number_parameters      367
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0930
_refine_ls_R_factor_gt            0.0455
_refine_ls_wR_factor_ref          0.0988
_refine_ls_wR_factor_gt           0.0859
_refine_ls_goodness_of_fit_ref    0.995
_refine_ls_restrained_S_all       0.995
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.5070(3) 0.12001(7) 0.2437(3) 0.0212(5) Uani 1 1 d . . .
C2 C 0.5967(3) 0.12234(7) 0.1404(3) 0.0203(5) Uani 1 1 d . . .
C3 C 0.6812(3) 0.08454(7) 0.1336(3) 0.0197(5) Uani 1 1 d . . .
C4 C 0.6536(3) 0.05318(7) 0.2295(3) 0.0204(5) Uani 1 1 d . . .
C5 C 0.5171(4) 0.15297(9) -0.1884(3) 0.0301(6) Uani 1 1 d . . .
C6 C 0.6401(5) 0.13237(9) -0.2520(4) 0.0367(7) Uani 1 1 d . . .
C7 C 0.6855(4) 0.08783(9) -0.1951(3) 0.0343(7) Uani 1 1 d . . .
C8 C 0.4023(3) 0.15216(7) 0.2802(3) 0.0204(5) Uani 1 1 d . . .
C9 C 0.4750(3) 0.19031(8) 0.3514(3) 0.0213(5) Uani 1 1 d . . .
C10 C 0.3746(3) 0.22165(8) 0.3760(3) 0.0228(6) Uani 1 1 d . . .
C11 C 0.1999(3) 0.21483(8) 0.3284(3) 0.0260(6) Uani 1 1 d . . .
C12 C 0.1268(4) 0.17711(8) 0.2608(3) 0.0271(6) Uani 1 1 d . . .
C13 C 0.2286(3) 0.14646(8) 0.2385(3) 0.0254(6) Uani 1 1 d . . .
C14 C 0.7260(4) 0.23296(9) 0.4524(5) 0.0345(7) Uani 1 1 d . . .
C15 C 0.1505(4) 0.28525(9) 0.3783(5) 0.0383(7) Uani 1 1 d . . .
C16 C 0.7102(3) 0.00968(7) 0.2464(3) 0.0202(5) Uani 1 1 d . . .
C17 C 0.7755(3) -0.01141(7) 0.4029(3) 0.0211(5) Uani 1 1 d . . .
C18 C 0.8452(3) -0.05095(8) 0.4158(3) 0.0230(6) Uani 1 1 d . . .
C19 C 0.8474(3) -0.07015(7) 0.2709(3) 0.0236(6) Uani 1 1 d . . .
C20 C 0.7721(3) -0.05109(8) 0.1124(3) 0.0252(6) Uani 1 1 d . . .
C21 C 0.7056(3) -0.01207(8) 0.1021(3) 0.0231(6) Uani 1 1 d . . .
C22 C 0.8457(4) -0.00998(9) 0.7039(3) 0.0262(6) Uani 1 1 d . . .
C23 C 1.0144(4) -0.12611(10) 0.4347(4) 0.0342(7) Uani 1 1 d . . .
O1 O 0.6476(2) 0.19363(5) 0.3971(2) 0.0254(4) Uani 1 1 d . . .
O2 O 0.0894(2) 0.24395(6) 0.3441(2) 0.0355(5) Uani 1 1 d . . .
O3 O 0.7682(2) 0.00925(5) 0.5405(2) 0.0273(4) Uani 1 1 d . . .
O4 O 0.9188(2) -0.10803(5) 0.2717(2) 0.0303(4) Uani 1 1 d . . .
S1 S 0.53068(8) 0.071700(19) 0.33656(8) 0.02254(16) Uani 1 1 d . . .
S2 S 0.60828(8) 0.168370(19) 0.03613(8) 0.02421(16) Uani 1 1 d . . .
S3 S 0.82324(8) 0.08053(2) 0.02867(8) 0.02570(17) Uani 1 1 d . . .
H1 H 0.649(3) 0.0009(7) -0.006(3) 0.008(5) Uiso 1 1 d . . .
H2 H 0.748(3) 0.0763(8) -0.253(3) 0.034(8) Uiso 1 1 d . . .
H3 H 0.180(3) 0.1218(8) 0.187(3) 0.022(7) Uiso 1 1 d . . .
H4 H 0.939(3) -0.1335(7) 0.490(3) 0.024(7) Uiso 1 1 d . . .
H5 H 0.827(3) 0.0083(8) 0.786(3) 0.028(7) Uiso 1 1 d . . .
H6 H 0.581(3) 0.0690(7) -0.218(3) 0.020(6) Uiso 1 1 d . . .
H7 H 0.969(3) -0.0140(7) 0.737(3) 0.018(6) Uiso 1 1 d . . .
H8 H 0.776(3) -0.0649(8) 0.014(3) 0.026(7) Uiso 1 1 d . . .
H9 H 0.889(3) -0.0650(7) 0.518(3) 0.012(6) Uiso 1 1 d . . .
H10 H 1.105(3) -0.1071(9) 0.507(3) 0.031(7) Uiso 1 1 d . . .
H11 H 0.796(4) -0.0356(9) 0.709(3) 0.043(8) Uiso 1 1 d . . .
H12 H 1.059(4) -0.1512(10) 0.407(4) 0.045(8) Uiso 1 1 d . . .
H13 H 0.245(4) 0.2870(8) 0.494(4) 0.045(8) Uiso 1 1 d . . .
H14 H 0.478(3) 0.1783(9) -0.247(3) 0.040(8) Uiso 1 1 d . . .
H15 H 0.671(4) 0.2543(9) 0.356(4) 0.047(9) Uiso 1 1 d . . .
H16 H 0.059(4) 0.3004(9) 0.384(3) 0.040(8) Uiso 1 1 d . . .
H17 H 0.584(4) 0.1320(8) -0.372(4) 0.042(8) Uiso 1 1 d . . .
H18 H 0.833(4) 0.2312(8) 0.460(3) 0.033(8) Uiso 1 1 d . . .
H19 H 0.727(3) 0.2390(9) 0.568(4) 0.043(8) Uiso 1 1 d . . .
H20 H 0.416(3) 0.1371(8) -0.206(3) 0.023(7) Uiso 1 1 d . . .
H21 H 0.185(4) 0.2939(9) 0.281(4) 0.057(10) Uiso 1 1 d . . .
H22 H 0.743(4) 0.1491(9) -0.220(3) 0.040(9) Uiso 1 1 d . . .
H23 H 0.428(3) 0.2466(9) 0.427(3) 0.036(8) Uiso 1 1 d . . .
H24 H 0.005(3) 0.1737(8) 0.227(3) 0.034(8) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.368(3) . ?
C1 C8 1.473(3) . ?
C1 S1 1.721(2) . ?
C2 C3 1.426(3) . ?
C2 S2 1.750(2) . ?
C3 C4 1.374(3) . ?
C3 S3 1.759(2) . ?
C4 C16 1.471(3) . ?
C4 S1 1.733(2) . ?
C5 C6 1.502(4) . ?
C5 S2 1.819(3) . ?
C5 H14 0.95(3) . ?
C5 H20 0.96(3) . ?
C6 C7 1.516(4) . ?
C6 H17 0.94(3) . ?
C6 H22 0.97(3) . ?
C7 S3 1.810(3) . ?
C7 H2 0.93(3) . ?
C7 H6 1.03(2) . ?
C8 C13 1.382(3) . ?
C8 C9 1.402(3) . ?
C9 O1 1.360(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.388(3) . ?
C10 H23 0.94(3) . ?
C11 O2 1.368(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.373(4) . ?
C12 H24 0.96(3) . ?
C13 H3 0.92(2) . ?
C14 O1 1.423(3) . ?
C14 H15 1.03(3) . ?
C14 H18 0.89(3) . ?
C14 H19 1.00(3) . ?
C15 O2 1.417(3) . ?
C15 H13 1.00(3) . ?
C15 H16 0.93(3) . ?
C15 H21 1.02(3) . ?
C16 C17 1.397(3) . ?
C16 C21 1.397(3) . ?
C17 O3 1.366(3) . ?
C17 C18 1.391(3) . ?
C18 C19 1.383(3) . ?
C18 H9 0.92(2) . ?
C19 O4 1.362(3) . ?
C19 C20 1.384(3) . ?
C20 C21 1.368(3) . ?
C20 H8 0.96(2) . ?
C21 H1 0.95(2) . ?
C22 O3 1.421(3) . ?
C22 H5 0.97(3) . ?
C22 H7 0.98(2) . ?
C22 H11 0.94(3) . ?
C23 O4 1.423(3) . ?
C23 H4 0.96(2) . ?
C23 H10 0.99(3) . ?
C23 H12 0.96(3) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C8 128.8(2) . . ?
C2 C1 S1 110.38(18) . . ?
C8 C1 S1 120.85(17) . . ?
C1 C2 C3 113.1(2) . . ?
C1 C2 S2 121.68(18) . . ?
C3 C2 S2 125.22(18) . . ?
C4 C3 C2 113.7(2) . . ?
C4 C3 S3 123.63(18) . . ?
C2 C3 S3 122.43(18) . . ?
C3 C4 C16 129.5(2) . . ?
C3 C4 S1 109.41(18) . . ?
C16 C4 S1 121.13(17) . . ?
C6 C5 S2 115.3(2) . . ?
C6 C5 H14 109.8(16) . . ?
S2 C5 H14 103.4(16) . . ?
C6 C5 H20 114.3(15) . . ?
S2 C5 H20 107.0(14) . . ?
H14 C5 H20 106(2) . . ?
C5 C6 C7 115.5(3) . . ?
C5 C6 H17 105.6(17) . . ?
C7 C6 H17 106.8(16) . . ?
C5 C6 H22 109.1(17) . . ?
C7 C6 H22 110.7(17) . . ?
H17 C6 H22 109(2) . . ?
C6 C7 S3 115.8(2) . . ?
C6 C7 H2 109.9(16) . . ?
S3 C7 H2 103.7(17) . . ?
C6 C7 H6 114.0(13) . . ?
S3 C7 H6 105.9(13) . . ?
H2 C7 H6 107(2) . . ?
C13 C8 C9 118.0(2) . . ?
C13 C8 C1 121.3(2) . . ?
C9 C8 C1 120.7(2) . . ?
O1 C9 C10 123.5(2) . . ?
O1 C9 C8 115.6(2) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C11 119.0(2) . . ?
C9 C10 H23 118.9(16) . . ?
C11 C10 H23 122.0(16) . . ?
O2 C11 C12 115.6(2) . . ?
O2 C11 C10 123.6(2) . . ?
C12 C11 C10 120.8(2) . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H24 122.1(16) . . ?
C11 C12 H24 118.7(16) . . ?
C12 C13 C8 122.1(2) . . ?
C12 C13 H3 119.7(15) . . ?
C8 C13 H3 118.1(15) . . ?
O1 C14 H15 109.2(16) . . ?
O1 C14 H18 107.4(18) . . ?
H15 C14 H18 104(2) . . ?
O1 C14 H19 108.6(16) . . ?
H15 C14 H19 118(2) . . ?
H18 C14 H19 109(2) . . ?
O2 C15 H13 110.1(16) . . ?
O2 C15 H16 105.2(18) . . ?
H13 C15 H16 106(2) . . ?
O2 C15 H21 106.7(17) . . ?
H13 C15 H21 114(2) . . ?
H16 C15 H21 114(2) . . ?
C17 C16 C21 116.8(2) . . ?
C17 C16 C4 123.3(2) . . ?
C21 C16 C4 119.8(2) . . ?
O3 C17 C18 122.7(2) . . ?
O3 C17 C16 116.1(2) . . ?
C18 C17 C16 121.2(2) . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H9 118.4(14) . . ?
C17 C18 H9 122.0(14) . . ?
O4 C19 C18 124.0(2) . . ?
O4 C19 C20 115.9(2) . . ?
C18 C19 C20 120.1(2) . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H8 121.8(15) . . ?
C19 C20 H8 118.5(15) . . ?
C20 C21 C16 122.5(2) . . ?
C20 C21 H1 120.4(13) . . ?
C16 C21 H1 117.0(13) . . ?
O3 C22 H5 107.0(14) . . ?
O3 C22 H7 111.7(13) . . ?
H5 C22 H7 109.3(19) . . ?
O3 C22 H11 112.7(17) . . ?
H5 C22 H11 108(2) . . ?
H7 C22 H11 108(2) . . ?
O4 C23 H4 110.1(15) . . ?
O4 C23 H10 110.7(15) . . ?
H4 C23 H10 111(2) . . ?
O4 C23 H12 103.4(17) . . ?
H4 C23 H12 108(2) . . ?
H10 C23 H12 113(2) . . ?
C9 O1 C14 118.3(2) . . ?
C11 O2 C15 117.2(2) . . ?
C17 O3 C22 117.44(19) . . ?
C19 O4 C23 117.0(2) . . ?
C1 S1 C4 93.36(12) . . ?
C2 S2 C5 102.22(12) . . ?
C3 S3 C7 103.53(13) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.46
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.296
_refine_diff_density_min   -0.326
_refine_diff_density_rms    0.070
